As messy as it is hilarious, Leslye Headland’s “Sleeping with Other People” is a great movie undermined by a misguided desire to be original. Headland — who also penned the screenplay — repeatedly excels at finding everyday moments of emotion and humor, but disappointingly squanders her characters’ evident charm on a wonky and ill-paced plot that tries too hard to update “When Harry Met Sally” for millennials.
Regardless of these minor gripes, however, Headland’s voice remains crystal clear throughout and, carried by a pair of first-rate performances from Jason Sudeikis and Alison Brie, “Sleeping with Other People” transcends its structural weaknesses, emerging as a fun, touching and delightfully vulgar rom-com-dram about the oft-frayed line between friends and lovers.
Jake (Sudeikis) and Lainey (Brie) first meet when they unceremoniously lose their virginity to each other atop a rooftop at Columbia. Nearly a decade later, they randomly re-connect when they both attend a sex addicts’ meeting after being shamed and dumped by their significant others. After an awkward attempt at a first date, the two soon reach an agreement to subtract sex from the equation, deciding that the pursuit of hedonism is not worth the risk of sabotaging the beginnings of an exquisite camaraderie. Naturally, as is standard for rom-coms of this ilk, the pair’s vow of chastity is soon endangered, as sexual tension and quasi-romantic shenanigans arise.
As far as plot goes, the rest is a shade confused. Major developments occur either too early or late, with Jake and Lainey refusing to compromise their pact even as their reasons for doing so become ever the more muddled. A third act time jump emerges from nowhere with no discernible reason for existence — save for superfluous conflict — effectively undermining the preceding hour. And, most damningly, the ending proves wholly unearned, with Jake and Lainey — surprise, surprise — throwing caution to the wind, lighting their blood oath aflame and hitting the sack because, after vehemently denying the couple’s irresistible chemistry for more than an hour, Headland sacrifices her petty determination to be different for an all-too-tidy (though admittedly uplifting) conclusion. Fortunately, for a comedy as sharp and sweet as this, a sturdy plot is actually of markedly diminished importance.
Aided by Brie and Sudeikis’ natural affability, Headland succeeds in burying the failings of the film’s structure beneath a truckload of charisma and a sizable helping of witty repartee. As written, Jake and Lainey are fascinating creatures: smart, funny and refreshingly in touch with their emotions. Slinging insults and compliments like arrows, they’re magnetic in a way that makes it impossible to look away. In turn, the ill timing of their actions and some contrived motivations fade into obscurity, making for an altogether pleasant viewing experience.
“Sleeping with Other People” breaks no boundaries, but it remains a genuine and genuinely hilarious comedy, that, like its central characters, is fairly hard not to admire.
Contact Will Ferrer at wferrer ‘at’ stanford.edu.